The problem with that is Slack no longer needs a small segment of vocal users. They used to, but now they're a huge established company with plenty of service contracts across tons of industries.
I'm not sure how Oracle really squares with that theory. From what I've seen, courting executives can work pretty well for companies widely hated by users.
They can be vocal about getting people out all the want, won't make them effective at it, especially if most people don't understand why power text editor users hate WYSIWYGs. Once contracts are inked and the whole company gets hooked on something like Slack good luck getting it back out.